


Relationship Coach

by songofhell



Category: Supernatural
Genre: M/M
Language: English
Status: Completed
Published: 2017-06-12
Updated: 2017-06-12
Packaged: 2018-11-13 02:39:43
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,229
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11175282
Author URL: https://archiveofourown.org/users/songofhell/pseuds/songofhell
Summary: Sam's not entirely sure how he wound up in this position, but once again Crowley is coming to him for relationship advice. Even though he had never particularly wanted his brother dating the demon, he can't seem to get out of helping Crowley make it work between them. But helping Crowley through his current dilemma will require an extra dose of patience.





	Relationship Coach

“Moose, there you are!” Crowley declared as he walked into one of the bunker’s storage rooms to see the younger Winchester organizing files.

Sam sighed as he turned around to face Crowley. “What do you want, Crowley? I’m a little busy here.”

“With what? Spring cleaning? I need your help, it’s important.”

His tone caught Sam’s attention, and he straightened up, frowning slightly in concern. “What’s going on?”

“It’s about Dean,” Crowley started, earning an exasperated sigh from Sam.

Of course it was. Sam wasn’t sure why he had thought it could possibly be anything other than Crowley asking for advice about Dean – again. He understood to a point – he was Dean’s brother, so it only made sense that when Crowley needed some advice concerning him, he would go to Sam – but he hadn’t signed up to be Crowley’s relationship coach. This had been going on for over a year now, and it didn’t look like it’d be stopping anytime soon.

_“Oh, moose… is your brother around?”_

_Sam looked up from his book at the demon who had just appeared in the library. “No, he’s at the store. Why?”_

_“Just… wondering.” Crowley pursed his lips slightly, glancing around the room._

_He arched an eyebrow at him. “Can I help you with something?”_

_“Well, now that you mention it…” He walked over and took a seat at the table across from Sam. “What sorts of romantic gestures does Dean prefer?”_

_Sam’s eyebrows shot up, and he huffed out a surprised laugh. “Excuse me?”_

_“If one were to ask him out, what would be the best methods to woo him?” Crowley reiterated._

_“You… you want to ask out Dean?” he clarified._

_“Obviously. I just don’t know how best to get him to say yes, rather than stab me.”_

_“Don’t know if there’s a guarantee for that,” Sam laughed. “But pie and whiskey will at least help.”_

_“I need more than that. Come on moose, help me out a little.”_

And despite his better judgement, Sam had helped him – more to shut him up than anything, and because he had never expected Dean to actually say yes to him. But when Dean had come home one day to see that Crowley had set up a movie night for them, complete with all of Dean’s favorite snacks… well, Sam hadn’t been there to see how it played out, but the fact that Crowley was still there the next morning filled in the blanks.

It hadn’t stopped there, either. Since Sam’s advice had worked out so well the first time, Crowley kept coming back for more – gift ideas, date ideas, tips for making up after a fight, the best destination for an anniversary trip. Whenever Sam was sure that there couldn’t possibly be any other piece of advice that Crowley could need from him, he was always proven wrong. So, what could it possibly be this time?

“What now?” Sam sighed.

Crowley took a deep breath, seeming to be more nervous than usual. “I want to ask him to marry me.”

His jaw dropped, his eyes going wide. “What?” he asked, sure that he had heard wrong.

“I want to ask Dean to marry me,” he repeated slowly and deliberately.

“…Oh.” Sam nodded slowly as he processed the fact that Crowley was planning on proposing to his brother. “Right…. You’re sure?”

Crowley sighed, his eyes narrowing slightly. _“Yes,_ I am sure. Do you think I would choose to get married lightly?”

“No… I guess not.” He cleared his throat. “So, what do you need from me?”

“Your help picking out the ring would be nice. It’s not going to be easy to find a decent ring that he’ll be willing to wear.”

That was an understatement.

“What about this one?” Crowley indicated yet another insanely expensive ring that had a huge square ruby in the center and either edge lined with black diamonds.

Sam shook his head. “Dean would never wear that.”

“Fine. This one?” The next ring he indicated had intricate detailing along the sides, and in the center was a large, round black diamond, surrounded by rubies.

Instead of responding, Sam walked away to look in another display case. “Try something more like this,” he suggested once he found a plain, silver band.

Crowley walked over and looked down at the ring with a frown. “I’m not proposing with that – it’s cheap.”

“It’s over a hundred dollars!” he protested.

“Dean deserves better.” He turned away and walked back over to the more expensive cases.

“Crowley, Dean’s not gonna care how much you spend on a ring,” Sam pointed out as he followed him. “He likes more simple things.”

“This one’s simple.” He indicated a ring with silver edges and two tones of wood in the middle – one black and one a reddish-purple – with diamonds inlaid around the middle.

“Better,” he sighed. “But maybe something without diamonds.”

They looked around for another twenty minutes before Crowley called Sam over to his side. “This is it.” He pointed out a ring made out of silver meteorite, giving it an unusual texture, with a black strip running around the center that was a combination of dinosaur bone and quartz.

Sam grinned and nodded. “Perfect.”

He was surprised when Crowley was ready to part ways after getting the ring without even asking for advice on how to propose.

“I can figure out some things on my own,” he said when Sam asked about it.

Sam chuckled. “News to me. How’re you doing it, then?”

“A candlelit dinner complete with everything romantic.”

He raised his eyebrows slightly, but didn’t comment. If it was what Crowley wanted to do, then that worked, he supposed. Besides, it was nice not to have to give him advice on something for once. “Good luck.”

He didn’t find out until after Dean and Crowley were engaged that Crowley had been lying.

“So, he didn’t propose over dinner?” Sam asked as he and Dean sat together in the bunker, enjoying a couple of beers.

“No way.” Dean shook his head. “Too normal for us.”

“That was what I was thinking when he told me. How’d he do it, then?”

“It was actually pretty damn sappy,” Dean admitted as he set his beer down on the table. “He took me to Scotland, where he grew up – said that as much as he hated his human life, he wanted to share all of himself with me.”

“Damn.”

“Yeah.” He grinned as he looked down at the ring on his finger. “He proposed at the crossroads where he sold his soul.”

“Romantic,” Sam commented with a slight frown.

“Hey, if he hadn’t sold his soul, he never would’ve became Crowley, and I never would’ve met him.”

“That’s true, I guess.” He finished off his beer and set the empty bottle down. “So, you happy?”

“Yeah.” Dean nodded than a smile. “Happier than I have been in a long time.”

“Good.”

When Crowley had first asked Sam how he should ask out Dean, Sam never would have even considered that in less than two years Dean and Crowley would be engaged. If he had known, he might not have helped, but now, having seen how Crowley was with Dean and how happy he made him, he was glad that he had. If he got to see his brother smile, maybe being Crowley’s relationship coach wasn’t so bad.


End file.
